Breaking Safety at the Token Boundary: How BPE Tokenization Creates Exploitable Gaps in LLM Alignment

Character-level perturbations bypass safety alignment in modern LLMs despite leaving prompts human-readable. We identify and test a central structural mechanism: BPE tokenization fragments safety-critical words into sub-word pieces, and the three public alignment datasets we surveyed contain no intentionally fragmented inputs. The mechanism is a chain, tested end-to-end on five model families (Qwen-3-4B, Qwen-2.5-7B, Gemma-3-4B, Llama-3.1-8B, Mistral-7B). An optimization targeting safety-token fragmentation flips the first-token refusal trigger on 80-100% of refused HarmBench prompts, with 48% of those flips producing genuinely harmful outputs (per-model 29-65%; gap-vs-behavior ROC-AUC 0.66-0.98, pooled 0.84). Activation patching localizes the disrupted signal to the last ~30% of layers; an alignment-data scan finds zero fragmented prompts among 30,000 examples (positive-control recall ≥ 99% at attack-relevant intensities); and targeted-mutation experiments isolate safety words as the disruption locus. On the defense side, a 68-cell grid (55 trained checkpoints) shows that no DPO configuration achieves seed- and pool-stable ASR closure on the three families with closed pool-size confounds. SFT trained on fragmented prompts closes ASR on 3/5 families but only via global collapse that raises refusal on benign prompts as well, indicating the missing distribution is necessary but not sufficient under the LoRA-16 recipe we tested. To distinguish selective repair from global collapse, we introduce Conv-Benign, a candidate paired diagnostic. All ASR claims are 3-judge-calibrated (cell rankings stable across judges; absolute levels ±18pp; see App.~B.13).